Sex Overload at the Tipton

Chapter 1- Jesse McCartney/Maddie


It was an ordinary day.

Maddie had just ended her shift; Jesse McCartney was back in town for a singing gig.


Maddie crept around upstairs, looking for the pop star’s room. She was horny and needed some sex badly.


The second door on her left in the new hallway she entered called out to her. She knew it was his.

She crept inside and lightly dropped her purse on the floor before shutting and locking the door. She slipped off her shoes, undid her tie, and unbuttoned the first and last two buttons on her shirt, revealing her lower stomach and some ample cleavage. Her plaid mini skirt was sexy enough as it was.

She suddenly heard the sound of a shower stop and positioned herself in a sexy, seductive pose on the bed.

Not two seconds later, Jesse McCartney walked out of the bathroom, completely naked (hey, why would he need a towel in “complete privacy?”).

His eyes widened at the sight of this sultry teenage girl on his bed, but he had to admit, it sort of turned him on. He could see down her shirt.

Maddie was completely silent as she let him drink her in.

“Hey, you’re that candy counter girl,” Jesse said.

“Uh, yeah,” Maddie said, then turning her voice seductive and saying, “But I give sweeter candy than chocolate and gum.”

She smirked when she saw Jesse get hard. He made no move to cover himself.

“Well, I’d take your word for it, but I don’t have experience with this sweeter candy,” Jesse smirked.

“Well how about you give it a go?” Maddie suggested.

“I think I’d like that,” Jesse smirked, making his way over to the bed.

Once he sat down, Maddie pounced, straddling his bare waist, her knees on either side of him before grabbing his shoulders and crashing their lips together.

His hands were caught against her chest, not that he minded.

She let him squeeze and touch her D-cup boobs through the material of her shirt, his touch giving the smooth surface goose bumps and making her nipples harden.

They let out of the kiss for a moment and Jesse ripped off her shirt, revealing a sultry, lacy black bra.

He reached behind her and unclasped the bra with ease. She shrugged it off and threw it on the floor with her shirt.

She expected his hands to be cold and calloused, like Trevor’s had been, but no.

They were warm, soft, and gentle with her.

Maddie threw her head back and moaned.

“Yeah, you like that, don’t you baby?” Jesse asked in a husky tone.

She expected him to grab her roughly, but his touch remained gentle, his fingers wandering feather-light over her nipples, breast skin, and in her cleavage valley.

Maddie moaned in response.

He lightly pushed her off of him and motioned for her to lay back.

She followed his silent order and relaxed as he placed feather-light kisses on her legs, starting at her left knee.

When he came to her upper-thigh, he reached under her miniskirt and wrapped his index finger around the wet bottom of her black thong.

As he pulled it down, he placed kisses on her right leg.

He threw the thong on the floor and pulled off her skirt, leaving her completely naked, just like him.

Maddie pounced again, rolling them over so she was on top, her legs straddling his hips, kissing him like wild with tongue action and all.

She smiled to herself as she felt him get hard, his erection rising up, just touching her outer folds. It made her wet.

He flipped them over suddenly and started kissing down her neck, nibbling on her collarbone, and then placing feather-light kisses down into the valley between her boobs.

Jesse took one of Maddie’s coral pink tits in his mouth, drawing little circles with his tongue around her nipple until it got hard.

He did the same with her other one.

Then, he got down to her very wet and pink pussy.

He darted his tongue towards it, just barely brushing her outer folds, teasing her.

Maddie moaned and put her ankles over his shoulders, pulling him closer. He wrapped his arms around her thighs and licked and kissed inside her, flicking her clit every so often.

He crawled back up her, only to be rolled over.

She shimmied down him and took him in her mouth, fondling, sucking, and kissing like an expert.

She smiled when she heard his moan of pleasure and continued her work, earning several moans.

After a moment, she knew he was seconds away from coming.

Just to tease him, she stopped out of nowhere.

He looked down at her in confusion and slight frustration, but was only returned with a smirk.

“I say enough fun and games,” Jesse said, his green eyes narrowing, “I want that sweet treat.”

She crawled next to him, lay down on her back and opened her legs wide before saying, “Come and get it.”

Jesse climbed in front of her on his knees and placed his hands under her hips, lifting her up.

He then slowly and teasingly placed his 8-incher into her wet, cummy walls. Maddie lifted her ankles on Jesse’s shoulders, her feet touching behind his head.

“Don’t even think about going slow,” Maddie warned.

“I wasn’t,” Jesse smirked.

With that, he went into full speed on her, going so fast that the bed started shaking.

“Yes!” Maddie screamed. “Oh yeah! Right there! All the way! Fuck me harder! HARDER!”

He was getting hard while he was in her, making his eight inches grow to at least eight and a half.

With that extra half inch, he pounded her G-spot with each thrust, resulting in little jumps and squeals of pleasure. It turned him on more.

He leaned over slowly, somehow maintaining his speed, and started licking and kissing her boobs, biting down softly on her nipples every so often.

Her legs went from his shoulders to around his middle. She squeezed her legs tightly around him, trying to get him deeper inside her.

Maddie moaned, and her toes clenched and unclenched as she came towards the climax.

The two blonde teenagers moaned, groaned, and screamed as they came to the climax of their session, Jesse unleashing warm, salty, sticky loads of his seed into Maddie.

He slowed down, but didn’t stop.

The two panted as Maddie’s legs continued to help him pull and push in and out of her.

When he came to a stop, her legs grabbed around him tightly, holding him closer, his head rammed against her G-spot, causing her to come one last time on him.

After a moment of catching their breaths, she opened her legs.

He pulled out of her and wiped himself off with one of the sheets.

Maddie got off the bed and went by the door where she dropped her purse on the way in.

She picked the purse up, headed towards the bathroom, and said, “Get warmed up. I’m going to change into something sexy for you.”

With a wink, she disappeared behind the door.


Five minutes later, Maddie walked out in a barely-there black leather skimpy bra that exposed over three quarters of her gigantic boobs, and a black leather garter belt holding to leather straps that went around her mid-thigh.

Jesse suddenly reached under the bed and pulled out a large plastic bag.

“Search for something nice you like,” the pop star said, scooting the bag towards Maddie.
The other blonde reached out and looked around inside, her eyes widening with pleasure as she looked at the contents: dildos, vibrators, and some strange looking frosted glass 10-inch dick were among the variety.

She heard him shifting around as she looked inside the bag.

When she looked up, she saw him crouched on the floor.

In front of him was what looked like a glass box, held together by a thick metal frame. There were gizmos and contraptions and wires hooked up inside the box. There was an opening on the far left edge, a metal rod sticking out of the opening. Attached to the metal rod was a nine inch rubber lube.

“W-what is that?” Maddie asked.
“Something special,” Jesse said, “You know, a guy gets worn out sometimes, but a girl always wants more.”

“Are you saying that’s a fucking machine?” Maddie asked.

Jesse nodded with a smirk.

Maddie made her way over to it, but Jesse stopped her and said, “Best for last.”

“What do you want to do?” Maddie asked.

“Choose something from the bag and I’ll use it on you,” he replied.

Maddie shifted through the bag and pulled out what looked like a drill, but it had a hot pink ten inch rubber dildo attached to the drill spiral.

“I’d like this,” Maddie said, handing the toy to Jesse as she climbed on the bed.

She lay back against the pillows and spread her legs open wide.

Jesse climbed onto the bed and turned on the drill. The dildo spun like mad, the head whirling around.

He brought it down to her outer folds slowly, teasing her. She was practically dripping, she was so wet.

She expected him to put it in her slowly, but when it was a centimeter away from her opening, he shoved it inside her, ramming her G-spot hard.

She jumped a bit, exciting him.

He just let it spin in her for a moment, then he pushed and pulled it in and out of her slowly at first, then he went faster and faster, thrusting it hard so it hit her G-spot each and every time.

She was moaning and groaning and jumping and squealing and it turned him on so much.

He pushed it deep, deep inside of her so the head was rammed up against her G-spot, and turned the speed dial on the drill from fast to maximum.

It was spinning fast and having it rammed up in her G-spot made her jump and squeal and then, they came at the exact same time, her cum soaking the dildo, and his seed spilling onto the sheets.

Jesse took the drill out of her, and after she caught her breath, she pushed him on his back and straddled his chest, her opening less than two inches from his face. She started giving him a blow/hand job.

After a minute, she said, “Jesse, use the drill on me.”

He stuck the drill into her cave and she opened her legs wide, causing her cave to increase in size.

He turned the dial to the last location: overdrive.

Jesse let it spin inside her and then he pushed and pulled it in and out of her fast, and then he kept it near her G-spot and started pushing and pulling it back only half an inch, and then ramming it into her G-spot. He kept repeating that over and over, looking at how tight her ass got and loved the feeling of her jumping on him.

After five minutes, they both climaxed in sync, Jesse shooting a big load of warm, salty, sticky seed into Maddie’s mouth, and Maddie’s cum soaking the dildo so much, some of it spilled out on the drill and Jesse’s hand.

The two pulled off one another and Jesse licked his hand clean.


The next toy they used was the frosted glass dick.

Maddie reached for it when Jesse pulled it out of the bag, but he pushed her away and motioned for her to open her legs.

She followed his instruction and opened her legs as wide as she could, hoping to get her cave as large as she could.

Jesse slipped the glass inside her, the dick picking up temperature as it made its way to her G-spot.

Maddie didn’t ask how it was possible; she was loving it too much to care.

Soon, Jesse was thrusting it in and out of her as fast as he could.

On the last thrust, Jesse rammed it all the way into Maddie’s cunt, jamming the head against her G-spot.

The glass was at maximum temperature and the burning sensation in her G-spot made Maddie come.


The two teenagers got off the bed and Jesse scooted the fucking machine closer to Maddie with a nod.

Maddie pulled the vanity chair over to where the machine was and crouched over the dildo on the metal rod.

Slowly, Maddie lowered herself onto the fake dick and then sat herself down on the vanity chair. She then realized there were feet rests on the sides of the machine. She placed her feet there and held on to the arm rests of the chair, preparing herself for this once-in-a-lifetime experience.

Jesse flicked a switch on the side and the dick started moving, slowly at first, and not going all the way in her.

“Don’t tease me McCartney,” Maddie shot.

“Alright then, but you asked for it,” Jesse warned before turning a dial.

The dick gained speed very quickly and it was hitting her G-spot hard, making her jump and squeal.

She threw her head back and moaned and groaned in pleasure.

“Yes! Oh yes! Right there! Ugh! Fuck me! Yeah!” Maddie screamed.

After three minutes, Maddie climaxed with a scream.


After that, the two climbed back onto the bed.

Maddie opened her legs wide and Jesse gratefully lowered himself into her, going at full speed.

Instead of wrapping her legs around him, Maddie kept her legs open wide to give him more room.

He hit her G-spot repeatedly and smiled and moaned at her squeals and jumps.

“Fuck you right! You like this baby, yeah! Fuckin’ you senseless!” Jesse shouted as he somehow managed to go faster.

“Right there! That’s right! Fuck me Jesse!” Maddie shouted.

“I’m doing you bitch! Fuck yeah! You want more of this! I’m giving it to you! Frikin fuck you hard!” Jesse shouted.

The two climaxed and came together.

Jesse collapsed, but managed to fall to the side so he didn’t fall on Maddie.

Maddie’s legs were wrapped around his waist, holding him where he was.

He bucked his hips against hers a few more times, giving hard, rough thrusts.

The two, breathing hard, then fell asleep, him still inside of her, their bodies glistening with sweat.